Bernstein started working in the sports industry during the early years of The Upper Deck Company and as Director of Development for their memorabilia division Upper Deck Authenticated.

Bernstein's services were retained by Major League Soccer from 1995–97, where he acted as their head of licensing and created the league's merchandise program. MLS secured over 50 national partners and reached $50 million in MLS-licensed sales in just its second season.

Bernstein became a partner in Pro Access Group in 1997 and created a platform of marketing campaigns to mark significant achievements in sports history. He went on to represent Barry Sanders, Emmitt Smith, and Barry Bonds.